ECB-ART-47842
J Org Chem
2002 Oct 18;6721:7565-8. doi: 10.1021/jo025988p.
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Stereoselective synthesis of Neu5Acalpha(2-->5)Neu5Gc: the building block of oligo/poly(-->5-O(g)(lycolyl)Neu5Gcalpha2-->) chains in sea urchin egg cell surface glycoprotein.
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The synthesis of a sialic acid dimer derivative, Neu5Acalpha(2-->5)Neu5Gc, is described. The synthetic strategy is based on the use of allyl alcohol to achieve an exclusive alpha-sialylation product. The allyloxy group is also a latent glycolic acid that provides the subsequent coupling with neuraminate with minimal protection-deprotection manipulations.
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Genes referenced: LOC100887844 LOC115919910